Heaven Ain't Close
by Charlotte Reese
Summary: Dean can't sleep. Might turn into series of one-shots. May become slight Dean/OFC. Set in season three.


Seven months before he was set to go to hell, Dean Winchester lay awake on a bed in a motel somewhere in Nebraska.

Sam was out like a light, snoring like a beast and half-hanging out of his bed, leaving Dean alone with his ever-morbid thoughts. Thoughts of hell and Sam alone and how the whole damn thing started with their damn father and would hopefully end with him.

As the seconds ticked by and Dean grew more and more agitated, shifting positions and fidgeting disquietedly, he finally threw the covers off himself and sat up. He ran a hand down his face and sighed in annoyance. Sparing his rather large little brother a morose glance, he put on his boots and, leaving a quick note reading _'Couldn't sleep. Be back whenever.'_, he grabbed his jacket and slipped out into the darkness.

He didn't bother with the Impala; there was a good enough dive just down the block. Dean made his way down the cracked sidewalk, passing a drunk, two bums and a schnauzer, holding his breath against the stench.

He couldn't remember the last time he'd been so grateful to step into a bar and smell the disgusting mix of alcohol, sweat and vomit. Probably never, but tonight, God he needed the escape.

Dean stood by the doorway for a few seconds, scanning the place for an empty booth or interesting company.

Bunch of drunk bikers at the pool tables, couples making out, someone getting a lap dance…

He was about to give up and take a seat at the bar when someone finally caught his eye.

She sat in a booth with her legs crossed up on the seat, sipping something bright red from a martini glass. She wore a black hooded sweatshirt that looked as though she'd stolen it from an old boyfriend, a pair of worn jeans, and tan hiking boots. She stood out like a Styx fan at a Britney Spears concert, and that made her interesting.

Wasting no time, Dean made his way through the crowded bar and straight to the girl in the booth.

He stood in front of her, watching her as she finished off her drink. When she set the glass down she looked up at him questioningly.

"Something I can do for you?"

"Nah, just thought I'd offer to buy you another drink," Dean replied smoothly, slipping into his usual charm.

"Ha. No thanks, Casanova. I don't drink and fuck."

Dean was momentarily taken aback, but his usual swagger returned to him quickly and he flashed a smile at her. She rolled her eyes and he raised his hand defensively. "Hey, look, I wasn't trying to offend you. I just wanted to buy you a drink and maybe have some friendly conversation. So what do you say?"

She sighed. "Yeah, whatever. Think I'll need something a little stronger than another of these. Get me a screwdriver and then we'll talk."

Dean was happy to oblige, and headed for the bar, getting a screwdriver for himself as well. He wondered, for a moment, what the hell he was doing…he glanced back at the girl, who was fiddling with a napkin and tapping her fingers on the table. She wasn't the usual suspect, and this was not his usual game plan. But a break from the usual…felt right. At least for one night.

Back at the table, he handed her the drink and slid into the seat across from her, taking a sip of his own drink and then setting it aside.

She watched him with mild interest, and then put her drink on the table and her feet on the floor. She leaned onto the table toward Dean.

"So you're not trying to get into my pants. Why don't I believe that?"

He smirked at her. "Because that usually is how my late-night bar encounters end up. But trust me, it's always consensual."

She scoffed. "Oh, I'm sure. All right, so you're gonna lay on the charm, keep buying the drinks, and hope that once I'm totally smashed I'll go with you back to some skeevy motel room. Am I warm?"

"Uh, no, actually," Dean replied, slightly put off by her insinuation. "Hard as it is to believe, I'm not actually that big of an asshole. Like I said, consensual. And anyway, I don't know if you've looked around you, but there are plenty of women in here who wouldn't say no."

She looked around, laughing. "Right, right. The whores with no shame. That your type?" she asked, putting her chin in her hand. "Blonde, about 5'5'', Daisy Dukes and spiky heels. The kind of girl who never says no to a good time. Something like that?"

"Depends on your definition of a good time."

She quirked an eyebrow. "Oh?"

"I'm having a pretty good time right now, and last I checked, I don't even know your name, much less what you've got on under all that."

She laughed again, and then offered a hand. "Penn."

Dean paused, then offered her his first name. "Dean."

They shook hands and then fell silent for a moment, the quiet only slightly awkward.

"So that's a sweet name."

"What?"

"Dean as in James Dean. Kinda badass. You know, if you're into that sort of thing," Penn said nonchalantly, a smile playing around her mouth.

"I can see where this is going," Dean said, grabbing his drink and taking a gulp.

"I'll bet you can. The answer to the question which you did not ask is sometimes."

Dean set down the glass. "Sometimes."

"On occasion, I am into the badass type. Depends on how hot he is and what he drives. And a few other things."

"And this is when I ask what other things, Penn? And you say—"

"None of your business, Dean. And you say—"

"That your natural hair color?"

Penn raised her eyebrows. "What? Seriously?"

Dean smirked. "Threw you off, didn't it?"

"Yeah, actually. Pretty good."

"I thought so," he replied with a cheeky grin.

"Somehow I knew you were gonna say that." She quirked an eyebrow and took another swig from her glass. "So."

"So…you from around here?"

Penn blew some hair out of her eyes. "Nah. Neither are you."

"Nice guess."

"Please, I know a townie when I see one and you're far from it. You actually look like you spend a lot of time on the road."

"Yeah, story of my life," Dean replied, looking down at his glass.

She nodded in understanding. "I get that. I was an Army brat till my dad disappeared."

"Disappeared? In combat?"

"No, on leave. With his commanding officer."

Dean's eyebrows shot up. "Whoa."

"Yeah, best part about the whole thing was that his commanding officer's name was Eric." Penn chugged the rest of her drink and slammed the glass down, letting out a breathless laugh.

"Damn. That…sucks."

She sighed. "That pretty much sums it up in PG terms. So anyway, after he disappeared the Army classified him as a deserter and gave us his salary. We used it to get a place a few towns over and here I am, in this fine establishment, talking to a drifter at ass o'clock."

Dean had to prevent himself from choking on his drink. "And that's the word of the day."

"Way to steal my awesomeness," Penn replied lazily, throwing a napkin at him.

He tossed it back and she handed it to him. He looked up at her, confused.

"You should keep that," she told him.

"Oh yeah? Why?"

"'Cause I gotta go before I do something crazy, like sleep with you."

She winked at him and slid out of the booth, tossing a "See ya" over her shoulder and leaving the bar.

Upon inspection of the napkin, Dean grinned when he saw what was written on it:

__

555-1793

_Just in case I cut our 'friendly conversation' short. Thanks for the drink, Casanova._


End file.
